Water → HCID 54038351, compound

HRID 1196147Notes

Reaction equation

HRID 1196147 reaction equation
[Br:1][C:2]([CH:9]=[CH2:10])=[CH:3][O:4][Si](C)(C)C.[CH2:11]([O:13][CH:14](OCC)[CH3:15])[CH3:12].O>ClCCl.[Br-].[Zn+2].[Br-]>[Br:1][C:2](=[CH:3][CH2:4][CH:11]([O:13][CH2:14][CH3:15])[CH3:12])[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 962WaterHCID 7765AcetalHCID 53670473HCID 53670473, compound

Product 1

HCID 54038351HCID 54038351, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.21 g (10 mmoles) of 2-bromo-1-trimethylsiloxybut-1,3-diene in 30 ml of anhydrous dichloromethane are introduced into a 100 ml reactor traversed by a stream of nitrogen. 1.18 g (about 11 mmoles) of 1,1-diethoxyethane are slowly added and then 100 mg of anhydrous zinc bromide. After reaction for 10 minutes, 20 ml of water are added, the organic phase is collected, and the aqueous phase is extracted with 20 ml of dichloromethane. The dichloromethane fractions are combined and dried with 5 g of anhydrous magnesium sulfate. The solvent is eliminated by vacuum evaporation and the residue distilled, the boiling point of the product being 66° C. under 0.15 mm Hg. 1.72 g of product are obtained, representing a yield of 78%. The structure of the product obtained is confirmed by NMR analysis and mass spectrometry.

Workup

  1. customAfter reaction for 10 minutes
  2. customthe organic phase is collected
  3. extractionthe aqueous phase is extracted with 20 ml of dichloromethane
  4. dry with materialdried with 5 g of anhydrous magnesium sulfate
  5. customThe solvent is eliminated by vacuum evaporation
  6. distillationthe residue distilled
  7. custombeing 66° C. under 0.15 mm Hg

Sources & evidence

ORD record
ord-c949eb2c5236482aaf66815a7aa45bfe
Source dataset
uspto-grants-1992_05
Patent number
US05113007

Reaction notes

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